Diethyl sulfide

Last updated
Diethyl sulfide
DiethylSulfide-skeletal.svg
DiethylSulfide-spaceFill.png
Names
Preferred IUPAC name
(Ethylsulfanyl)ethane
Other names
  • 1,1-Thiobisethane
  • Diethyl thioether
  • Ethyl sulfide
  • Thioethyl ether
Identifiers
3D model (JSmol)
1696909
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.934 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-526-9
1915
KEGG
PubChem CID
RTECS number
  • LC7200000
UNII
  • InChI=1S/C4H10S/c1-3-5-4-2/h3-4H2,1-2H3 Yes check.svgY
    Key: LJSQFQKUNVCTIA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3
    Key: DENRZWYUOJLTMF-UHFFFAOYAR
  • InChI=1/C4H10S/c1-3-5-4-2/h3-4H2,1-2H3
    Key: LJSQFQKUNVCTIA-UHFFFAOYAZ
  • S(CC)CC
Properties
(CH3CH2)2S
Molar mass 90.18 g·mol−1
AppearanceColorless liquid
Odor Unpleasant
Density 0.837 g/cm3
Melting point −103.8 °C (−154.8 °F; 169.3 K)
Boiling point 92 °C (198 °F; 365 K)
insoluble
Solubility in ethanol miscible
Solubility in diethyl ether miscible
−67.9·10−6 cm3/mol
1.44233
Hazards [1]
Occupational safety and health (OHS/OSH):
Main hazards
Skin and eye irritant. Highly flammable liquid and vapor
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H315, H319
P210, P233, P264, P280, P303+P361+P353, P370+P378
NFPA 704 (fire diamond)
2
3
1
Flash point −10 °C (14 °F; 263 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related thioethers
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diethyl sulfide (British English: diethyl sulphide) is an organosulfur compound with the chemical formula (CH3CH2)2S. It is a colorless, malodorous liquid. Although a common thioether, it has few applications.

Contents

Preparation

Diethyl sulfide is a by-product of the commercial production of ethanethiol, which is prepared by the reaction of ethylene with hydrogen sulfide over an alumina-based catalyst. The amount of diethyl sulfide produced can be controlled by varying the ratio of hydrogen sulfide to ethylene.

Occurrence

Diethyl sulfide has been found to be a constituent of the odor of durian fruit [2] and as a constituent found in volatiles from potatoes. [3]

Reactions

Diethyl sulfide is a Lewis base, classified as a soft ligand (see also ECW model). Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots. [4] [5]

With bromine, it forms a salt called diethylbromosulfonium bromide: [6]

(CH3CH2)2S + Br2[(CH3CH2)2SBr]+Br

A typical coordination complex is cis-PtCl2(S(CH2CH3)2)2.

Structure of cis-PtCl2(SEt2)2. CIKXIE.png
Structure of cis-PtCl2(SEt2)2.

Related Research Articles

<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<span class="mw-page-title-main">Bromine</span> Chemical element, symbol Br and atomic number 35

Bromine is a chemical element with the symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.

<span class="mw-page-title-main">Thiol</span> Any organic compound having a sulfanyl group (–SH)

In organic chemistry, a thiol, or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol".

<span class="mw-page-title-main">Sulfide (organic)</span> Organic compound with an –S– group

In organic chemistry, an organic sulfide or thioether is an organosulfur functional group with the connectivity R−S−R' as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

<span class="mw-page-title-main">1,2-Dibromoethane</span> Chemical compound

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2
H
4
Br
2
. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm, and is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.

1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. It is used in the perfume industry.

<span class="mw-page-title-main">Ethanethiol</span> Chemical compound

Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with sulfur in place of oxygen. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic in high concentrations. It occurs naturally as a minor component of petroleum, and may be added to otherwise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

<i>n</i>-Butyllithium Chemical compound

n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.

Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. The simplest thioether, it is a flammable liquid that boils at 37 °C (99 °F) and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize, cabbage, beetroot, and seafoods. It is also an indication of bacterial contamination in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol.

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

An inorganic nonaqueous solvent is a solvent other than water, that is not an organic compound. These solvents are used in chemical research and industry for reactions that cannot occur in aqueous solutions or require a special environment. Inorganic nonaqueous solvents can be classified into two groups, protic solvents and aprotic solvents. Early studies on inorganic nonaqueous solvents evaluated ammonia, hydrogen fluoride, sulfuric acid, as well as more specialized solvents, hydrazine, and selenium oxychloride.

<span class="mw-page-title-main">Adduct</span> Product of direct addition of two or more distinct molecules

An adduct is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is considered a distinct molecular species. Examples include the addition of sodium bisulfite to an aldehyde to give a sulfonate. It can be considered as a single product resulting from the direct combination of different molecules which comprises all atoms of the reactant molecules.

<span class="mw-page-title-main">Phenethyl alcohol</span> Chemical compound

Phenethyl alcohol, or 2-phenylethanol, is an organic compound with the chemical formula C6H5CH2CH2OH. It is a colourless liquid with a pleasant floral odor. It occurs widely in nature, being found in a variety of essential oils. It is slightly soluble in water, but miscible with most organic solvents. The molecule of phenethyl alcohol consists of a phenethyl group attached to a hydroxyl group.

Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

<i>tert</i>-Butylthiol Chemical compound

tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.

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<span class="mw-page-title-main">1-Octanol</span> Chemical compound

1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils. It is used to evaluate the lipophilicity of pharmaceutical products.

<span class="mw-page-title-main">Ethane-1,1-dithiol</span> Chemical compound

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In chemistry, the ECW model is a semi-quantitative model that describes and predicts the strength of Lewis acid–Lewis base interactions. Many chemical reactions can be described as acid–base reactions, so models for such interactions are of potentially broad interest. The model initially assigned E and C parameters to each and every acid and base. The model was later expanded to the ECW model to cover reactions that have a constant energy term, W, which describes processes that precede the acid–base reaction. This quantitative model is often discussed with the qualitative HSAB theory, which also seeks to rationalize the behavior of diverse acids and bases.

References

  1. "GESTIS-Stoffdatenbank". gestis.dguv.de (in German).
  2. Baldry, Jane; J. Dougan; G. E. Howard (1972). "Volatile Flavouring Constituents of Durian". Phytochemistry. 11 (6): 2081–2084. Bibcode:1972PChem..11.2081B. doi:10.1016/s0031-9422(00)90176-6.
  3. Gumbmann, M. R.; H. K. Burr (1964). "Food Flavors and Odors, Volatile Sulfur Compounds in Potatoes". Journal of Agricultural and Food Chemistry. 12 (5): 404–408. doi:10.1021/jf60135a004.
  4. Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9
  5. Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". Journal of Chemical Education. 54: 612–613. doi:10.1021/ed054p612. The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model.
  6. Scott A. Snyder, Daniel S. Treitler (2011). "Synthesis of Et2SBrSbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations". Organic Syntheses. 88: 54. doi:10.15227/orgsyn.088.0054.
  7. C.Hansson (2007). "cis-Dichloridobis(diethyl sulfide-κS)platinum(II) at 295 and 150 K". Acta Crystallographica Section C. 63 (Pt 8): m361-3. doi:10.1107/S0108270107030417. PMID   17675684.